Process of preparing para&#39;-hydroxy-ortho-benzoyl benzoic-acid



Patented Dec. 27, 1927.

UNITED STATES PATENT OFFICE.

IVAN GUBELMANN, HENRY J. WEILAND, AND OTTO STALLMANN, OF SOUTH MILWAU- KEE, WISCONSIN, ASSIGNORS TO THE NEWPORT GOMPAN Y, O]? CARROLLVILLE, WISCONSIN, 'A CORPORATION OF DELAWARE.

PROCESS OF PREPARING PARA' HYDROXY-ORTI-IO BENZOYL BENZOIG-AOID.

No Drawing.

This invention relates to a method of preparing para-hydroxy-ortho-benzoyl-benzoicacid. 'We have discovered that para-hydroxyortho-benzoyl-benzoic acid may be prepared by treating para'-halogen-orthobenzoyl-benzoic acid, or its salts, in a water or alcoholic solution with alkaline reacting substances. This reaction proceeds at a reasonable rate at elevated temperatures, the rate of reaction increasing in proportion to the temperature. In carrying out the reaction, any suitable alkaline reacting substance may be used, such as caustic soda or potash, sodium or potassium carbonateor the like, all of these alkaline substances giving the same end product.

The general reaction may be expressed by the following chemical equation, in which M represents a metallic radical and hlg repre sents a halogen element:

+ 3MOH =0 from hot water.

in which parts by weight are given illus-.

trates the application of our invention in the preferred form:

A mixture of 130 parts of crude parachloro-ortho-benzoyl-benzoic acid, 600 parts of water and 66parts of sodium hydroxide in the form of a 4,0" B. solution is heated in an autoclave to150-200 G. for a period of 12 hours. The pressure is maintained between 100 and 200 pounds per square inch...

At the end of this period, the reaction mass, which is a clear ellow solution,afber cooling down is slow y run into a mixture consisting of 1000 parts of ice, 1000 parts of droxyl grou Application filed November 29, 1926. Serial No. 151,590.

water and 75 parts of sulfuric acid B.). The precipitated product is now filtered OE and driedat 100 C. The yield is 115 parts, corresponding to 95% of theory, with a melting point on the crude of 209 to 210 C.

Upon recrystallization from hot water, the

- ortho-benzoyl-benzoic acid and its salts with an alkaline reacting substance, whereby the halogen is split OE and replaced by an hyaccompanied by the formation of alkali halide.

. 2. The process of reparing para-hydroxy-ortho-benzoylenzoic acid, which comprises treating ;para-chloro-ortho-ben zoyl-benzoic acid with an alkaline reacting substance, whereby the chlorine atom is replaced by an hydroxyl group accompanied by the formation of alkali chloride.

3. The process of preparing para'-hy droxy ortho benzoyl benzoic acid, which comprises treating para-chloro-ortho-benzoyl-benzoic acid with caustic alkali, whereby the chlorine atom is replaced by an hy- A drox 1 group accompanied by the formation of al ali chloride,

4. The process of preparing para -hysplit ofi" to form alkali chloride and replaced by an hydroxyl grou 5. The process o preparing pa ra'-hydrox'y ortho -benzoy1- benzoic acid which longed period of time, cooling and precipitatcomprises heating approximately two parts ing out the product.

of para'-chloro 0rth0-benz0yl-benzoic acid In testimony whereof We have hereunto 10 with one part of caustic alkali in the form subscribed our names.

5 of its water solution at a temperature of be- IVAN GUBELMANN.

tween 150 and 200 C. and at .a pressure of HENRY J. \VEILAND.

100 to 200 pounds persquare inch for a pro- OTTO STALLMANN. 

